Tryptophan methyl ester: a proposal of the thermal decomposition mechanism

Tryptophan (Trp) is a secondary metabolite derived from the shikimate pathway responsible for the synthesis of several alkaloids in some animals and plants. In mammalian metabolism, Trp participates in several biological functions and has a wide application in drug synthesis. In this work, Trp was used as a starting material for the synthesis of its methyl ester derivative. This compound was characterized by the NMR H-1 e C-13, FTIR, TG-DTA, TG-DSC coupled to FTIR, and HPLC/MS techniques. The preliminary tests showed a formation of the tryptophan methyl ester (Z3) as the main product. The thermal behavior of Z3 showed significant changes when compared to its precursor. From the data obtained through thermoanalytical techniques, it was possible to determine a thermal decomposition mechanism for tryptophan methyl ester, as well as isolating and characterizing the intermediary obtained in the first thermal decomposition step, tryptamine. Compound Z3 and intermediate compounds from its thermal decomposition were optimized by molecular modeling, and the theoretical FTIR spectrum of the compounds showed a good correlation with experimental data.

Automated summary

Tryptophan is a secondary metabolite derived from the shikimate pathway and plays a key role in the synthesis of alkaloids in some animals and plants. It is widely utilized in drug synthesis and exhibits various biological functions in mammalian metabolism. The thermal behavior and decomposition mechanism of the tryptophan methyl ester compound were investigated using thermoanalytical techniques, with intermediate products characterized and optimized through molecular modeling.